#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:19:29 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558235.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_1558235
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            'C17.55 H15.55 N2.45 O2'
_chemical_formula_weight         292.77
_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             2020-03-10T15:57:04-00:00
_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                93.0700(16)
_cell_angle_beta                 107.0652(11)
_cell_angle_gamma                114.2729(11)
_cell_formula_units_Z            2
_cell_length_a                   8.07233(10)
_cell_length_b                   9.87774(15)
_cell_length_c                   10.88779(14)
_cell_measurement_reflns_used    15546
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      77.192
_cell_measurement_theta_min      4.307
_cell_volume                     741.29(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      230(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 0.964
_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      0.0004882
_diffrn_orient_matrix_UB_12      0.0477696
_diffrn_orient_matrix_UB_13      -0.148104
_diffrn_orient_matrix_UB_21      -0.0733325
_diffrn_orient_matrix_UB_22      0.1679051
_diffrn_orient_matrix_UB_23      0.0100898
_diffrn_orient_matrix_UB_31      0.2001872
_diffrn_orient_matrix_UB_32      -0.003876
_diffrn_orient_matrix_UB_33      -0.0279718
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.964
_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            27752
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.335
_diffrn_reflns_theta_min         4.335
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.52
_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    1.312
_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         0.161
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0041(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   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3038
_refine_ls_number_restraints     306
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0364
_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)+(0.0605P)²+0.0803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.108
_reflns_Friedel_coverage         0
_reflns_number_gt                2721
_reflns_number_total             3038
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b2.cif
_cod_data_source_block           A25_BE75_230
_cod_original_cell_volume        741.293(19)
_cod_database_code               1558235
_shelx_estimated_absorpt_t_min   0.858
_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 0.16609(11) 0.15717(9) 0.30653(7) 0.0482(2) Uani 1 1 d . . . . .
H1 H 0.198771 0.184278 0.386937 0.072 Uiso 1 1 calc R U . . .
O2 O 0.82282(12) 0.22830(10) 0.43188(8) 0.0551(2) Uani 1 1 d . . . . .
H2A H 0.827394 0.266018 0.503493 0.083 Uiso 1 1 calc R U . . .
N1 N 0.26084(14) 0.24708(12) 0.57126(9) 0.0492(2) Uani 1 1 d . . . . .
N2A N 0.234(4) 0.379(2) 0.941(2) 0.039(2) Uani 0.197(3) 1 d D U P A 1
N3A N 0.272(4) 0.507(2) 0.995(2) 0.043(3) Uani 0.197(3) 1 d D U P A 1
C17 C 0.2137(12) 0.3788(7) 0.9340(6) 0.0407(10) Uani 0.776(3) 1 d D U P A 2
H17 H 0.156133 0.300524 0.975558 0.049 Uiso 0.776(3) 1 calc DR U P A 2
C18 C 0.2645(11) 0.5196(7) 0.9867(6) 0.0379(7) Uani 0.776(3) 1 d D U P A 2
H18 H 0.322327 0.598214 0.94552 0.045 Uiso 0.776(3) 1 calc R U P A 2
N2B N 0.264(5) 0.464(4) 0.920(3) 0.042(3) Uani 0.0278(16) 1 d D U P A 3
N3B N 0.193(5) 0.412(4) 1.004(3) 0.044(3) Uani 0.0278(16) 1 d D U P A 3
N4 N 0.17555(13) 0.65118(11) 1.33267(9) 0.0458(2) Uani 1 1 d . . . . .
C1 C 0.31684(16) 0.15362(11) 0.27774(10) 0.0395(2) Uani 1 1 d . . . . .
C2 C 0.49423(16) 0.19161(11) 0.37414(9) 0.0397(2) Uani 1 1 d . . . . .
H2 H 0.511407 0.21933 0.46258 0.048 Uiso 1 1 calc R U . . .
C3 C 0.64682(16) 0.18898(12) 0.34089(10) 0.0422(3) Uani 1 1 d . . . . .
C4 C 0.62031(19) 0.14518(12) 0.20966(11) 0.0481(3) Uani 1 1 d . . . . .
H4 H 0.721795 0.141636 0.18614 0.058 Uiso 1 1 calc R U . . .
C5 C 0.44287(19) 0.10723(12) 0.11516(10) 0.0498(3) Uani 1 1 d . . . . .
H5 H 0.425042 0.078404 0.026766 0.06 Uiso 1 1 calc R U . . .
C6 C 0.29049(18) 0.11041(12) 0.14683(10) 0.0466(3) Uani 1 1 d . . . . .
H6 H 0.170642 0.083756 0.080865 0.056 Uiso 1 1 calc R U . . .
C7 C 0.32215(17) 0.39335(14) 0.62040(11) 0.0494(3) Uani 1 1 d . . . . .
H7 H 0.370728 0.465213 0.570944 0.059 Uiso 1 1 calc R U . . .
C8 C 0.31825(17) 0.44464(13) 0.73888(11) 0.0462(3) Uani 1 1 d . . . . .
H8 H 0.365162 0.548869 0.769628 0.055 Uiso 1 1 calc R U . . .
C9 C 0.24360(15) 0.33969(12) 0.81289(10) 0.0401(2) Uani 1 1 d D . . . .
C10 C 0.18391(17) 0.18828(13) 0.76348(11) 0.0468(3) Uani 1 1 d . . . . .
H10 H 0.135931 0.113898 0.811116 0.056 Uiso 1 1 calc R U . . .
C11 C 0.19529(17) 0.14750(13) 0.64428(11) 0.0496(3) Uani 1 1 d . . . . .
H11 H 0.154896 0.044472 0.612835 0.059 Uiso 1 1 calc R U . . .
C12 C 0.23350(15) 0.55736(12) 1.10772(10) 0.0397(2) Uani 1 1 d D . . . .
C13 C 0.28681(17) 0.70799(13) 1.15261(11) 0.0469(3) Uani 1 1 d . . . . .
H13 H 0.343675 0.782004 1.107342 0.056 Uiso 1 1 calc R U . . .
C14 C 0.25649(18) 0.74939(13) 1.26368(11) 0.0494(3) Uani 1 1 d . . . . .
H14 H 0.294988 0.852665 1.292531 0.059 Uiso 1 1 calc R U . . .
C15 C 0.12265(16) 0.50497(13) 1.28945(10) 0.0451(3) Uani 1 1 d . . . . .
H15 H 0.064762 0.433616 1.336344 0.054 Uiso 1 1 calc R U . . .
C16 C 0.14885(17) 0.45357(12) 1.17930(11) 0.0442(3) Uani 1 1 d . . . . .
H16 H 0.110031 0.349757 1.152909 0.053 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 -6 0.0412
-4 -4 -5 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 116.91(10) . . ?
N3A N2A C9 125.7(19) . . ?
N2A N3A C12 131.1(19) . . ?
C18 C17 C9 122.5(5) . . ?
C18 C17 H17 118.8 . . ?
C9 C17 H17 118.8 . . ?
C17 C18 C12 122.0(5) . . ?
C17 C18 H18 119 . . ?
C12 C18 H18 119 . . ?
N3B N2B C9 113(3) . . ?
N2B N3B C12 106(3) . . ?
C14 N4 C15 116.85(10) . . ?
O1 C1 C2 122.04(9) . . ?
O1 C1 C6 118.21(10) . . ?
C2 C1 C6 119.75(10) . . ?
C1 C2 C3 120.52(9) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.15(9) . . ?
O2 C3 C4 118.09(10) . . ?
C2 C3 C4 119.76(10) . . ?
C5 C4 C3 118.96(11) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.84(10) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.17(11) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C8 123.87(11) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 119.03(11) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 117.17(10) . . ?
C10 C9 N2A 118.2(8) . . ?
C8 C9 N2A 124.5(8) . . ?
C10 C9 C17 118.7(3) . . ?
C8 C9 C17 124.0(3) . . ?
C10 C9 N2B 149.8(11) . . ?
C8 C9 N2B 93.0(11) . . ?
C11 C10 C9 119.72(11) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N1 C11 C10 123.25(11) . . ?
N1 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
C13 C12 C16 116.98(10) . . ?
C13 C12 N3A 122.5(8) . . ?
C16 C12 N3A 120.5(8) . . ?
C13 C12 C18 117.4(3) . . ?
C16 C12 C18 125.6(3) . . ?
C13 C12 N3B 155.7(10) . . ?
C16 C12 N3B 87.0(10) . . ?
C14 C13 C12 119.87(10) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N4 C14 C13 123.64(11) . . ?
N4 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
N4 C15 C16 123.33(10) . . ?
N4 C15 H15 118.3 . . ?
C16 C15 H15 118.3 . . ?
C15 C16 C12 119.33(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 1.3558(13) . ?
O1 H1 0.83 . ?
O2 C3 1.3527(14) . ?
O2 H2A 0.83 . ?
N1 C11 1.3351(16) . ?
N1 C7 1.3389(15) . ?
N2A N3A 1.236(10) . ?
N2A C9 1.463(17) . ?
N3A C12 1.464(16) . ?
C17 C18 1.319(4) . ?
C17 C9 1.468(5) . ?
C17 H17 0.94 . ?
C18 C12 1.468(5) . ?
C18 H18 0.94 . ?
N2B N3B 1.244(10) . ?
N2B C9 1.57(4) . ?
N3B C12 1.64(4) . ?
N4 C14 1.3331(15) . ?
N4 C15 1.3386(15) . ?
C1 C2 1.3881(15) . ?
C1 C6 1.3933(14) . ?
C2 C3 1.3914(15) . ?
C2 H2 0.94 . ?
C3 C4 1.3974(15) . ?
C4 C5 1.3795(18) . ?
C4 H4 0.94 . ?
C5 C6 1.3830(18) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3743(16) . ?
C7 H7 0.94 . ?
C8 C9 1.3957(16) . ?
C8 H8 0.94 . ?
C9 C10 1.3883(15) . ?
C10 C11 1.3782(16) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.3820(16) . ?
C12 C16 1.3955(15) . ?
C13 C14 1.3757(16) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C16 1.3831(15) . ?
C15 H15 0.94 . ?
C16 H16 0.94 . ?
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 0.83 1.92 2.7485(12) 176.8 . yes
O2 H2A N4 0.83 1.93 2.7622(12) 177.2 2_667 yes
