#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:19:29 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558233.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_1558233
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            'C17.54 H15.54 N2.46 O2'
_chemical_formula_weight         292.78
_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             2020-03-10T15:58:33-00:00
_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                93.2450(18)
_cell_angle_beta                 107.0364(13)
_cell_angle_gamma                114.2057(13)
_cell_formula_units_Z            2
_cell_length_a                   8.10962(13)
_cell_length_b                   9.89822(18)
_cell_length_c                   10.89834(15)
_cell_measurement_reflns_used    14206
_cell_measurement_temperature    270(2)
_cell_measurement_theta_max      75.685
_cell_measurement_theta_min      4.308
_cell_volume                     747.06(2)
_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      270(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.959
_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      0.0006697
_diffrn_orient_matrix_UB_12      0.0482059
_diffrn_orient_matrix_UB_13      -0.1481174
_diffrn_orient_matrix_UB_21      -0.0735467
_diffrn_orient_matrix_UB_22      0.167412
_diffrn_orient_matrix_UB_23      0.0101517
_diffrn_orient_matrix_UB_31      0.1992293
_diffrn_orient_matrix_UB_32      -0.0039657
_diffrn_orient_matrix_UB_33      -0.0274327
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       8
_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            27405
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.418
_diffrn_reflns_theta_min         4.333
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.521
_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    1.302
_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         0.18
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0042(9)
_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     242
_refine_ls_number_reflns         3053
_refine_ls_number_restraints     306
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0381
_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)+(0.0623P)²+0.0687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1141
_reflns_Friedel_coverage         0
_reflns_number_gt                2643
_reflns_number_total             3053
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b2.cif
_cod_data_source_block           A25_BE75_270
_cod_database_code               1558233
_shelx_estimated_absorpt_t_min   0.859
_shelx_estimated_absorpt_t_max   0.943
_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 0.16690(12) 0.15542(10) 0.30661(8) 0.0584(2) Uani 1 1 d . . . . .
H1 H 0.198638 0.181299 0.386091 0.088 Uiso 1 1 calc R U . . .
O2 O 0.82075(13) 0.22779(12) 0.43130(8) 0.0669(3) Uani 1 1 d . . . . .
H2A H 0.824716 0.263777 0.502361 0.1 Uiso 1 1 calc R U . . .
N1 N 0.26051(15) 0.24652(13) 0.57121(10) 0.0584(3) Uani 1 1 d . . . . .
N2A N 0.241(4) 0.385(3) 0.941(2) 0.047(2) Uani 0.167(3) 1 d D U P A 1
N3A N 0.274(5) 0.510(3) 0.997(2) 0.052(3) Uani 0.167(3) 1 d D U P A 1
C17 C 0.2132(9) 0.3774(7) 0.9340(5) 0.0472(9) Uani 0.771(3) 1 d D U P A 2
H17 H 0.156953 0.299836 0.974737 0.057 Uiso 0.771(3) 1 calc DR U P A 2
C18 C 0.2637(11) 0.5180(7) 0.9863(6) 0.0457(7) Uani 0.771(3) 1 d D U P A 2
H18 H 0.320333 0.595263 0.945435 0.055 Uiso 0.771(3) 1 calc R U P A 2
N2B N 0.269(2) 0.466(2) 0.9200(15) 0.050(3) Uani 0.0618(18) 1 d D U P A 3
N3B N 0.197(2) 0.410(2) 1.0029(16) 0.052(3) Uani 0.0618(18) 1 d D U P A 3
N4 N 0.17665(14) 0.65111(12) 1.33260(9) 0.0544(3) Uani 1 1 d . . . . .
C1 C 0.31733(17) 0.15246(11) 0.27775(10) 0.0470(3) Uani 1 1 d . . . . .
C2 C 0.49363(16) 0.19034(12) 0.37381(10) 0.0473(3) Uani 1 1 d . . . . .
H2 H 0.510476 0.217329 0.461346 0.057 Uiso 1 1 calc R U . . .
C3 C 0.64541(18) 0.18833(13) 0.34045(11) 0.0506(3) Uani 1 1 d . . . . .
C4 C 0.6192(2) 0.14487(14) 0.20943(12) 0.0574(3) Uani 1 1 d . . . . .
H4 H 0.719184 0.141537 0.186049 0.069 Uiso 1 1 calc R U . . .
C5 C 0.4428(2) 0.10703(14) 0.11538(11) 0.0597(3) Uani 1 1 d . . . . .
H5 H 0.425351 0.078758 0.027927 0.072 Uiso 1 1 calc R U . . .
C6 C 0.29116(19) 0.10976(13) 0.14685(11) 0.0555(3) Uani 1 1 d . . . . .
H6 H 0.173194 0.083461 0.081594 0.067 Uiso 1 1 calc R U . . .
C7 C 0.32174(19) 0.39260(15) 0.61995(12) 0.0594(3) Uani 1 1 d . . . . .
H7 H 0.369506 0.463088 0.570875 0.071 Uiso 1 1 calc R U . . .
C8 C 0.31816(19) 0.44458(14) 0.73832(12) 0.0563(3) Uani 1 1 d . . . . .
H8 H 0.364517 0.547607 0.768565 0.068 Uiso 1 1 calc R U . . .
C9 C 0.24415(16) 0.34076(13) 0.81225(11) 0.0488(3) Uani 1 1 d D . . . .
C10 C 0.18480(19) 0.19008(14) 0.76333(12) 0.0564(3) Uani 1 1 d . . . . .
H10 H 0.137957 0.117147 0.810747 0.068 Uiso 1 1 calc R U . . .
C11 C 0.19521(19) 0.14839(15) 0.64452(12) 0.0588(3) Uani 1 1 d . . . . .
H11 H 0.154588 0.046396 0.613624 0.071 Uiso 1 1 calc R U . . .
C12 C 0.23291(16) 0.55618(14) 1.10802(11) 0.0490(3) Uani 1 1 d D . . . .
C13 C 0.28621(18) 0.70602(14) 1.15271(12) 0.0569(3) Uani 1 1 d . . . . .
H13 H 0.342276 0.778773 1.107928 0.068 Uiso 1 1 calc R U . . .
C14 C 0.25655(19) 0.74787(14) 1.26331(12) 0.0591(3) Uani 1 1 d . . . . .
H14 H 0.29454 0.849975 1.29156 0.071 Uiso 1 1 calc R U . . .
C15 C 0.12342(18) 0.50520(14) 1.28980(11) 0.0543(3) Uani 1 1 d . . . . .
H15 H 0.066499 0.435213 1.336331 0.065 Uiso 1 1 calc R U . . .
C16 C 0.14893(18) 0.45318(14) 1.17947(12) 0.0541(3) Uani 1 1 d . . . . .
H16 H 0.110433 0.350587 1.15334 0.065 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
3 6 0 0.0565
-2 0 6 0.0536
1 6 1 0.0529
0 -6 -1 0.0564
5 2 3 0.1012
-5 -5 -1 0.093
0 6 4 0.0506
0 0 7 0.0473
-4 2 0 0.1051
1 -4 3 0.0582
-3 -4 3 0.0674
-1 -1 -7 0.0394
0 -3 5 0.0488
0 3 6 0.0455
-1 -4 -7 0.0412
-4 -4 -6 0.0836
-1 -6 -4 0.0452
3 6 4 0.0661
-3 3 -3 0.0956
-5 -2 -3 0.1148
4 5 1 0.0716
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 116.71(10) . . ?
N3A N2A C9 130(2) . . ?
N2A N3A C12 133(2) . . ?
C18 C17 C9 121.3(5) . . ?
C18 C17 H17 119.4 . . ?
C9 C17 H17 119.4 . . ?
C17 C18 C12 121.8(5) . . ?
C17 C18 H18 119.1 . . ?
C12 C18 H18 119.1 . . ?
N3B N2B C9 112.0(17) . . ?
N2B N3B C12 105.9(15) . . ?
C14 N4 C15 116.81(10) . . ?
O1 C1 C2 122.12(9) . . ?
O1 C1 C6 118.15(11) . . ?
C2 C1 C6 119.74(11) . . ?
C1 C2 C3 120.53(10) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.16(10) . . ?
O2 C3 C4 118.02(11) . . ?
C2 C3 C4 119.82(11) . . ?
C5 C4 C3 118.82(12) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.05(10) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.03(12) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.81(12) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 119.02(12) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 117.18(11) . . ?
C10 C9 N2A 119.7(10) . . ?
C8 C9 N2A 122.9(10) . . ?
C10 C9 C17 117.4(3) . . ?
C8 C9 C17 125.3(3) . . ?
C10 C9 N2B 149.7(6) . . ?
C8 C9 N2B 93.1(6) . . ?
C11 C10 C9 119.82(11) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N1 C11 C10 123.40(12) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C13 C12 C16 117.03(11) . . ?
C13 C12 N3A 121.1(10) . . ?
C16 C12 N3A 121.8(10) . . ?
C13 C12 C18 117.2(3) . . ?
C16 C12 C18 125.7(3) . . ?
C13 C12 N3B 155.0(5) . . ?
C16 C12 N3B 87.9(5) . . ?
C14 C13 C12 119.89(11) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N4 C14 C13 123.85(12) . . ?
N4 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
N4 C15 C16 123.14(11) . . ?
N4 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C12 119.28(11) . . ?
C15 C16 H16 120.4 . . ?
C12 C16 H16 120.4 . . ?
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 1.3569(14) . ?
O1 H1 0.82 . ?
O2 C3 1.3530(15) . ?
O2 H2A 0.82 . ?
N1 C11 1.3327(17) . ?
N1 C7 1.3376(16) . ?
N2A N3A 1.234(10) . ?
N2A C9 1.453(18) . ?
N3A C12 1.442(18) . ?
C17 C18 1.317(4) . ?
C17 C9 1.473(5) . ?
C17 H17 0.93 . ?
C18 C12 1.477(4) . ?
C18 H18 0.93 . ?
N2B N3B 1.245(10) . ?
N2B C9 1.563(18) . ?
N3B C12 1.660(18) . ?
N4 C14 1.3293(17) . ?
N4 C15 1.3358(16) . ?
C1 C2 1.3855(16) . ?
C1 C6 1.3927(15) . ?
C2 C3 1.3890(17) . ?
C2 H2 0.93 . ?
C3 C4 1.3953(15) . ?
C4 C5 1.3766(19) . ?
C4 H4 0.93 . ?
C5 C6 1.3802(19) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.3744(17) . ?
C7 H7 0.93 . ?
C8 C9 1.3917(17) . ?
C8 H8 0.93 . ?
C9 C10 1.3826(17) . ?
C10 C11 1.3733(17) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.3758(17) . ?
C12 C16 1.3931(17) . ?
C13 C14 1.3702(18) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?
C15 C16 1.3845(17) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?
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 2.7508(13) 176.3 . yes
O2 H2A N4 0.82 1.95 2.7669(13) 177.5 2_667 yes
