#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558215.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_1558215
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            'C18.01 H15.51 N2 O2'
_chemical_formula_weight         291.94
_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             2020-04-01T11:39:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                92.8705(14)
_cell_angle_beta                 107.4858(10)
_cell_angle_gamma                114.3213(12)
_cell_formula_units_Z            2
_cell_length_a                   8.16783(10)
_cell_length_b                   9.90151(16)
_cell_length_c                   10.91446(11)
_cell_measurement_reflns_used    17030
_cell_measurement_temperature    270(2)
_cell_measurement_theta_max      76.898
_cell_measurement_theta_min      4.327
_cell_volume                     751.69(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      270(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_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      -0.009491
_diffrn_orient_matrix_UB_12      -0.104915
_diffrn_orient_matrix_UB_13      -0.1137767
_diffrn_orient_matrix_UB_21      -0.2208704
_diffrn_orient_matrix_UB_22      -0.0780316
_diffrn_orient_matrix_UB_23      -0.0451788
_diffrn_orient_matrix_UB_31      -0.0082619
_diffrn_orient_matrix_UB_32      0.115205
_diffrn_orient_matrix_UB_33      -0.08847
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            28189
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.307
_diffrn_reflns_theta_min         4.334
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.91455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.29
_exptl_crystal_description       block
_exptl_crystal_F_000             307
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.03
_refine_ls_extinction_coef       0.0050(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   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3100
_refine_ls_number_restraints     579
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0348
_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)+(0.0546P)²+0.0621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1015
_reflns_Friedel_coverage         0
_reflns_number_gt                2761
_reflns_number_total             3100
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           BE75_BA25_270
_cod_original_cell_volume        751.686(19)
_cod_database_code               1558215
_shelx_estimated_absorpt_t_min   0.889
_shelx_estimated_absorpt_t_max   0.956
_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 0.16800(10) 0.15138(9) 0.30476(7) 0.0573(2) Uani 1 1 d . . . . .
H1 H 0.199662 0.176029 0.384327 0.086 Uiso 1 1 calc R U . . .
O2 O 0.81962(11) 0.22525(10) 0.43111(8) 0.0658(2) Uani 1 1 d . . . . .
H2A H 0.82333 0.259613 0.502368 0.099 Uiso 1 1 calc R U . . .
N1 N 0.26157(13) 0.24443(11) -0.43154(9) 0.0573(2) Uani 1 1 d . . . . .
C1 C 0.31784(14) 0.14969(10) 0.27609(9) 0.0460(2) Uani 1 1 d . . . . .
C2 C 0.49347(14) 0.18722(10) 0.37268(9) 0.0465(2) Uani 1 1 d . . . . .
H2 H 0.51023 0.213234 0.460181 0.056 Uiso 1 1 calc R U . . .
C3 C 0.64484(15) 0.18628(11) 0.33981(10) 0.0494(2) Uani 1 1 d . . . . .
C4 C 0.61874(17) 0.14468(12) 0.20880(10) 0.0571(3) Uani 1 1 d . . . . .
H4 H 0.718439 0.142375 0.18573 0.069 Uiso 1 1 calc R U . . .
C5 C 0.44325(18) 0.10713(13) 0.11427(10) 0.0598(3) Uani 1 1 d . . . . .
H5 H 0.425824 0.079888 0.026825 0.072 Uiso 1 1 calc R U . . .
C6 C 0.29196(17) 0.10872(12) 0.14548(10) 0.0549(3) Uani 1 1 d . . . . .
H6 H 0.174421 0.082708 0.079939 0.066 Uiso 1 1 calc R U . . .
C7 C 0.19673(16) 0.14783(13) -0.35727(11) 0.0573(3) Uani 1 1 d . . . . .
H7 H 0.155872 0.045571 -0.38685 0.069 Uiso 1 1 calc R U . . .
C8 C 0.18700(16) 0.19136(13) -0.23908(10) 0.0544(3) Uani 1 1 d . . . . .
H8 H 0.139616 0.119239 -0.191146 0.065 Uiso 1 1 calc R U . . .
C9 C 0.24784(14) 0.34266(12) -0.19160(10) 0.0488(2) Uani 1 1 d D U . . .
C10 C 0.32118(16) 0.44453(13) -0.26653(11) 0.0563(3) Uani 1 1 d . . . . .
H10 H 0.368122 0.547813 -0.237451 0.068 Uiso 1 1 calc R U . . .
C11 C 0.32359(16) 0.39095(14) -0.38423(11) 0.0590(3) Uani 1 1 d . . . . .
H11 H 0.371145 0.460636 -0.433953 0.071 Uiso 1 1 calc R U . . .
C12A C 0.2184(6) 0.3779(3) -0.0668(4) 0.0429(6) Uani 0.674(7) 1 d D U P A 1
H12A H 0.164674 0.298657 -0.026732 0.051 Uiso 0.674(7) 1 calc R U P A 1
C13A C 0.2661(3) 0.5183(3) -0.0110(2) 0.0413(5) Uani 0.674(7) 1 d D U P A 1
H13A H 0.324013 0.596157 -0.050931 0.05 Uiso 0.674(7) 1 calc R U P A 1
C12B C 0.274(4) 0.453(2) -0.083(2) 0.050(3) Uani 0.081(7) 1 d D U P A 2
H12B H 0.350751 0.55381 -0.078889 0.06 Uiso 0.081(7) 1 calc R U P A 2
C13B C 0.202(3) 0.424(2) 0.007(2) 0.050(3) Uani 0.081(7) 1 d D U P A 2
H13B H 0.128983 0.321135 0.001872 0.059 Uiso 0.081(7) 1 calc R U P A 2
C14A C 0.2343(8) 0.5610(4) 0.1105(4) 0.0397(8) Uani 0.674(7) 1 d DG U P A 1
C15A C 0.1503(8) 0.4535(3) 0.1782(4) 0.0467(8) Uani 0.674(7) 1 d G U P A 1
H15A H 0.11455 0.352062 0.149428 0.056 Uiso 0.674(7) 1 calc R U P A 1
C16A C 0.1199(8) 0.4977(4) 0.2890(4) 0.0466(9) Uani 0.674(7) 1 d G U P A 1
H16A H 0.063708 0.425779 0.3343 0.056 Uiso 0.674(7) 1 calc R U P A 1
N2A N 0.1734(8) 0.6494(4) 0.3320(4) 0.0483(11) Uani 0.674(7) 1 d G U P A 1
C17A C 0.2574(8) 0.7569(3) 0.2643(4) 0.0485(8) Uani 0.674(7) 1 d G U P A 1
H17A H 0.293157 0.858337 0.293059 0.058 Uiso 0.674(7) 1 calc R U P A 1
C18A C 0.2878(8) 0.7127(4) 0.1535(4) 0.0461(8) Uani 0.674(7) 1 d G U P A 1
H18A H 0.344 0.784622 0.108186 0.055 Uiso 0.674(7) 1 calc R U P A 1
C14B C 0.2125(18) 0.5223(12) 0.1170(9) 0.0531(19) Uani 0.326(7) 1 d D U P A 2
C15B C 0.1307(19) 0.4467(9) 0.2020(11) 0.0556(17) Uani 0.326(7) 1 d . U P A 2
H15B H 0.081158 0.342028 0.190512 0.067 Uiso 0.326(7) 1 calc R U P A 2
C16B C 0.1235(19) 0.5282(12) 0.3034(10) 0.0500(16) Uani 0.326(7) 1 d . U P A 2
H16B H 0.063152 0.468725 0.354871 0.06 Uiso 0.326(7) 1 calc R U P A 2
N2B N 0.1797(19) 0.6614(11) 0.3394(10) 0.060(2) Uani 0.326(7) 1 d . U P A 2
C17B C 0.2527(17) 0.7249(11) 0.2621(11) 0.0548(16) Uani 0.326(7) 1 d . U P A 2
H17B H 0.302239 0.829667 0.281828 0.066 Uiso 0.326(7) 1 calc R U P A 2
C18B C 0.2758(16) 0.6736(11) 0.1534(10) 0.0513(16) Uani 0.326(7) 1 d . U P A 2
H18B H 0.33368 0.740465 0.105276 0.062 Uiso 0.326(7) 1 calc R U P A 2
C19 C 0.245(2) 0.4082(18) -0.0783(14) 0.063(3) Uani 0.25 1 d D U P A 2
C20 C 0.2419(18) 0.4699(19) 0.0121(9) 0.068(2) Uani 0.25 1 d D U P A 2
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
2 -6 0 0.0556
-2 6 0 0.0503
1 -5 4 0.0717
-5 1 1 0.0337
5 -1 -1 0.0318
-2 -3 -2 0.0622
5 -2 -4 0.0659
2 3 2 0.0477
1 1 -7 0.0688
-1 5 -5 0.0636
5 -5 0 0.0498
-3 0 -4 0.0609
0 -3 6 0.0788
2 -2 5 0.0662
2 5 -1 0.0374
-1 5 3 0.0598
-4 5 -2 0.0542
2 2 3 0.0581
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 . . ?
C7 N1 C11 116.58(9) . . ?
O1 C1 C2 121.98(8) . . ?
O1 C1 C6 118.28(9) . . ?
C2 C1 C6 119.74(10) . . ?
C1 C2 C3 120.52(9) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.23(9) . . ?
O2 C3 C4 118.01(10) . . ?
C2 C3 C4 119.76(10) . . ?
C5 C4 C3 118.94(10) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.90(9) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.13(10) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C8 123.40(10) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.87(10) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C19 C9 C8 128.7(7) . . ?
C19 C9 C10 114.3(7) . . ?
C8 C9 C10 117.05(9) . . ?
C19 C9 C12B 16.3(5) . . ?
C8 C9 C12B 144.9(7) . . ?
C10 C9 C12B 98.0(7) . . ?
C8 C9 C12A 115.94(14) . . ?
C10 C9 C12A 126.94(15) . . ?
C11 C10 C9 119.18(10) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.87(11) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13A C12A C9 122.6(3) . . ?
C13A C12A H12A 118.7 . . ?
C9 C12A H12A 118.7 . . ?
C12A C13A C14A 125.5(2) . . ?
C12A C13A H13A 117.2 . . ?
C14A C13A H13A 117.2 . . ?
C13B C12B C9 127(2) . . ?
C13B C12B H12B 116.5 . . ?
C9 C12B H12B 116.5 . . ?
C12B C13B C14B 132(2) . . ?
C12B C13B H13B 114.1 . . ?
C14B C13B H13B 114.1 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 121.9(2) . . ?
C18A C14A C13A 118.1(2) . . ?
C16A C15A C14A 120 . . ?
C16A C15A H15A 120 . . ?
C14A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A C16A H16A 120 . . ?
C16A N2A C17A 120 . . ?
C18A C17A N2A 120 . . ?
C18A C17A H17A 120 . . ?
N2A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C20 C14B C18B 119.2(9) . . ?
C20 C14B C15B 130.6(8) . . ?
C18B C14B C15B 110.1(5) . . ?
C20 C14B C13B 16.8(5) . . ?
C18B C14B C13B 135.3(9) . . ?
C15B C14B C13B 114.4(8) . . ?
C16B C15B C14B 118.9(5) . . ?
C16B C15B H15B 120.6 . . ?
C14B C15B H15B 120.6 . . ?
N2B C16B C15B 132.8(6) . . ?
N2B C16B C17B 37.2(3) . . ?
C15B C16B C17B 95.6(4) . . ?
N2B C16B H16B 113.6 . . ?
C15B C16B H16B 113.6 . . ?
C17B C16B H16B 150.8 . . ?
C16B N2B C17B 106.5(6) . . ?
N2B C17B C18B 133.2(7) . . ?
N2B C17B C16B 36.3(4) . . ?
C18B C17B C16B 96.9(5) . . ?
N2B C17B H17B 113.4 . . ?
C18B C17B H17B 113.4 . . ?
C16B C17B H17B 149.7 . . ?
C14B C18B C17B 118.5(5) . . ?
C14B C18B H18B 120.7 . . ?
C17B C18B H18B 120.7 . . ?
C20 C19 C9 176(2) . . ?
C19 C20 C14B 171(2) . . ?
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 1.3574(12) . ?
O1 H1 0.82 . ?
O2 C3 1.3538(13) . ?
O2 H2A 0.82 . ?
N1 C7 1.3307(15) . ?
N1 C11 1.3381(15) . ?
C1 C2 1.3857(14) . ?
C1 C6 1.3899(13) . ?
C2 C3 1.3903(14) . ?
C2 H2 0.93 . ?
C3 C4 1.3948(14) . ?
C4 C5 1.3752(17) . ?
C4 H4 0.93 . ?
C5 C6 1.3826(16) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.3749(15) . ?
C7 H7 0.93 . ?
C8 C9 1.3835(15) . ?
C8 H8 0.93 . ?
C9 C19 1.379(12) . ?
C9 C10 1.3872(16) . ?
C9 C12B 1.475(17) . ?
C9 C12A 1.501(3) . ?
C10 C11 1.3740(16) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12A C13A 1.335(4) . ?
C12A H12A 0.93 . ?
C13A C14A 1.499(3) . ?
C13A H13A 0.93 . ?
C12B C13B 1.271(18) . ?
C12B H12B 0.93 . ?
C13B C14B 1.466(16) . ?
C13B H13B 0.93 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.93 . ?
C16A N2A 1.39 . ?
C16A H16A 0.93 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.93 . ?
C18A H18A 0.93 . ?
C14B C20 1.358(11) . ?
C14B C18B 1.359(8) . ?
C14B C15B 1.378(8) . ?
C15B C16B 1.367(8) . ?
C15B H15B 0.93 . ?
C16B N2B 1.203(8) . ?
C16B C17B 1.948(13) . ?
C16B H16B 0.93 . ?
N2B C17B 1.229(7) . ?
C17B C18B 1.362(7) . ?
C17B H17B 0.93 . ?
C18B H18B 0.93 . ?
C19 C20 1.146(14) . ?
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 0.82 1.93 2.7476(11) 174.9 1_556 yes
O2 H2A N2A^a 0.82 1.97 2.79(2) 176.5 2_666 yes
O2 H2A N2B^b 0.82 1.87 2.690(8) 177.1 2_666 yes
