#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:19:29 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558251.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_1558251
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            'C16.46 H14.46 N3.54 O2'
_chemical_formula_weight         293.86
_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             2020-03-12T16:26:45-00:00
_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                94.0306(12)
_cell_angle_beta                 106.4496(13)
_cell_angle_gamma                113.6558(14)
_cell_formula_units_Z            2
_cell_length_a                   8.04776(11)
_cell_length_b                   9.80445(15)
_cell_length_c                   10.87711(16)
_cell_measurement_reflns_used    11987
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      75.381
_cell_measurement_theta_min      4.305
_cell_volume                     737.25(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      air
_diffrn_ambient_temperature      290(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 0.969
_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      -0.0289254
_diffrn_orient_matrix_UB_12      -0.1655213
_diffrn_orient_matrix_UB_13      -0.0032032
_diffrn_orient_matrix_UB_21      -0.0990228
_diffrn_orient_matrix_UB_22      -0.0386061
_diffrn_orient_matrix_UB_23      -0.1499409
_diffrn_orient_matrix_UB_31      0.1969073
_diffrn_orient_matrix_UB_32      0.0434529
_diffrn_orient_matrix_UB_33      -0.0177724
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_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            27841
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.209
_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    0.735
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.659
_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 yellow'
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0051(11)
_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   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3036
_refine_ls_number_restraints     306
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0433
_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)+(0.0693P)²+0.0779P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1308
_reflns_Friedel_coverage         0
_reflns_number_gt                2556
_reflns_number_total             3036
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b2.cif
_cod_data_source_block           A75_BE25_290
_cod_database_code               1558251
_shelx_estimated_absorpt_t_min   0.856
_shelx_estimated_absorpt_t_max   0.96
_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 0.16621(14) 0.15727(12) 0.31178(9) 0.0642(3) Uani 1 1 d . . . . .
H1 H 0.197149 0.182119 0.391486 0.096 Uiso 1 1 calc R U . . .
O2 O 0.81971(15) 0.22252(14) 0.43349(10) 0.0751(3) Uani 1 1 d . . . . .
H2A H 0.823381 0.258646 0.505071 0.113 Uiso 1 1 calc R U . . .
N1 N 0.25980(17) 0.24845(14) 0.57913(11) 0.0617(3) Uani 1 1 d . . . . .
N2A N 0.213(2) 0.3765(9) 0.9425(9) 0.0543(10) Uani 0.645(3) 1 d D U P A 1
N3A N 0.2687(13) 0.5136(8) 0.9823(6) 0.0529(8) Uani 0.645(3) 1 d D U P A 1
C17 C 0.219(7) 0.381(3) 0.940(3) 0.054(3) Uani 0.229(3) 1 d D U P A 2
H17 H 0.17316 0.30262 0.982603 0.065 Uiso 0.229(3) 1 calc R U P A 2
C18 C 0.255(4) 0.519(3) 0.9943(19) 0.054(2) Uani 0.229(3) 1 d D U P A 2
H18 H 0.300343 0.598283 0.952089 0.064 Uiso 0.229(3) 1 calc DR U P A 2
N2B N 0.2791(15) 0.4714(15) 0.9278(11) 0.058(2) Uani 0.126(2) 1 d D U P A 3
N3B N 0.1906(15) 0.4029(13) 0.9977(11) 0.0579(19) Uani 0.126(2) 1 d D U P A 3
N4 N 0.17741(17) 0.64978(14) 1.32806(11) 0.0594(3) Uani 1 1 d . . . . .
C1 C 0.3174(2) 0.15329(13) 0.28186(12) 0.0518(3) Uani 1 1 d . . . . .
C2 C 0.49240(19) 0.18806(14) 0.37742(12) 0.0528(3) Uani 1 1 d . . . . .
H2 H 0.508174 0.21352 0.465325 0.063 Uiso 1 1 calc R U . . .
C3 C 0.6447(2) 0.18519(15) 0.34289(13) 0.0559(3) Uani 1 1 d . . . . .
C4 C 0.6200(2) 0.14350(16) 0.21188(14) 0.0631(4) Uani 1 1 d . . . . .
H4 H 0.719912 0.138682 0.187901 0.076 Uiso 1 1 calc R U . . .
C5 C 0.4450(2) 0.10943(16) 0.11812(13) 0.0651(4) Uani 1 1 d . . . . .
H5 H 0.428782 0.08288 0.030278 0.078 Uiso 1 1 calc R U . . .
C6 C 0.2930(2) 0.11350(16) 0.15054(13) 0.0614(4) Uani 1 1 d . . . . .
H6 H 0.17608 0.089981 0.085535 0.074 Uiso 1 1 calc R U . . .
C7 C 0.3234(2) 0.39613(17) 0.62838(15) 0.0656(4) Uani 1 1 d . . . . .
H7 H 0.372706 0.466369 0.579587 0.079 Uiso 1 1 calc R U . . .
C8 C 0.3197(2) 0.44981(17) 0.74759(15) 0.0636(4) Uani 1 1 d . . . . .
H8 H 0.366596 0.553646 0.778884 0.076 Uiso 1 1 calc DR U . . .
C9 C 0.2443(2) 0.34518(16) 0.81963(13) 0.0557(3) Uani 1 1 d D . . . .
C10 C 0.1823(2) 0.19334(17) 0.77106(14) 0.0622(4) Uani 1 1 d . . . . .
H10 H 0.134056 0.120734 0.818339 0.075 Uiso 1 1 calc R U . . .
C11 C 0.1929(2) 0.15063(17) 0.65186(14) 0.0631(4) Uani 1 1 d . . . . .
H11 H 0.150887 0.047605 0.620067 0.076 Uiso 1 1 calc R U . . .
C12 C 0.2305(2) 0.54994(18) 1.10374(13) 0.0583(3) Uani 1 1 d D . . . .
C13 C 0.2854(2) 0.70048(18) 1.14679(15) 0.0663(4) Uani 1 1 d . . . . .
H13 H 0.341213 0.771941 1.100924 0.08 Uiso 1 1 calc R U . . .
C14 C 0.2577(2) 0.74522(17) 1.25790(15) 0.0660(4) Uani 1 1 d . . . . .
H14 H 0.29724 0.848566 1.286315 0.079 Uiso 1 1 calc R U . . .
C15 C 0.1217(2) 0.50210(17) 1.28585(14) 0.0606(3) Uani 1 1 d . . . . .
H15 H 0.064322 0.43335 1.333108 0.073 Uiso 1 1 calc R U . . .
C16 C 0.1455(2) 0.44659(17) 1.17437(14) 0.0631(4) Uani 1 1 d . . . . .
H16 H 0.105777 0.342925 1.14757 0.076 Uiso 1 1 calc R 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 6 -1 0.055
0 4 4 0.0525
0 -6 2 0.0757
3 -6 0 0.0674
5 -1 0 0.0887
5 0 -3 0.0947
0 0 7 0.026
0 0 -7 0.0283
-2 -3 -2 0.0761
-5 0 3 0.0919
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 117.03(12) . . ?
N3A N2A C9 112.3(6) . . ?
N2A N3A C12 114.0(5) . . ?
C18 C17 C9 124.1(19) . . ?
C18 C17 H17 117.9 . . ?
C9 C17 H17 117.9 . . ?
C12 C18 C17 123.3(18) . . ?
C12 C18 H18 118.4 . . ?
C17 C18 H18 118.4 . . ?
N3B N2B C9 104.1(12) . . ?
N2B N3B C12 99.0(10) . . ?
C14 N4 C15 117.22(12) . . ?
O1 C1 C2 122.10(11) . . ?
O1 C1 C6 118.11(12) . . ?
C2 C1 C6 119.79(13) . . ?
C1 C2 C3 120.44(11) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C4 118.02(13) . . ?
O2 C3 C2 122.10(11) . . ?
C4 C3 C2 119.88(13) . . ?
C5 C4 C3 118.88(13) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.99(12) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.98(14) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.47(14) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 118.29(14) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C10 C9 C8 118.64(13) . . ?
C10 C9 C17 116.2(12) . . ?
C8 C9 C17 125.1(12) . . ?
C10 C9 N2A 114.2(4) . . ?
C8 C9 N2A 127.1(3) . . ?
C10 C9 N2B 149.8(4) . . ?
C8 C9 N2B 91.5(4) . . ?
C11 C10 C9 118.94(14) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N1 C11 C10 123.59(13) . . ?
N1 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
C18 C12 C13 114.2(12) . . ?
C18 C12 C16 127.1(12) . . ?
C13 C12 C16 118.56(13) . . ?
C13 C12 N3A 114.9(3) . . ?
C16 C12 N3A 126.5(3) . . ?
C13 C12 N3B 154.0(3) . . ?
C16 C12 N3B 87.2(3) . . ?
C12 C13 C14 119.24(14) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
N4 C14 C13 123.88(14) . . ?
N4 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
N4 C15 C16 122.79(14) . . ?
N4 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C15 C16 C12 118.32(14) . . ?
C15 C16 H16 120.8 . . ?
C12 C16 H16 120.8 . . ?
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 1.3593(16) . ?
O1 H1 0.82 . ?
O2 C3 1.3560(17) . ?
O2 H2A 0.82 . ?
N1 C11 1.3301(19) . ?
N1 C7 1.3366(19) . ?
N2A N3A 1.232(4) . ?
N2A C9 1.464(6) . ?
N3A C12 1.490(4) . ?
C17 C18 1.317(10) . ?
C17 C9 1.42(2) . ?
C17 H17 0.93 . ?
C18 C12 1.294(9) . ?
C18 H18 0.93 . ?
N2B N3B 1.237(9) . ?
N2B C9 1.525(13) . ?
N3B C12 1.643(13) . ?
N4 C14 1.330(2) . ?
N4 C15 1.3331(18) . ?
C1 C2 1.3844(19) . ?
C1 C6 1.3902(18) . ?
C2 C3 1.3894(19) . ?
C2 H2 0.93 . ?
C3 C4 1.3891(18) . ?
C4 C5 1.377(2) . ?
C4 H4 0.93 . ?
C5 C6 1.380(2) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.378(2) . ?
C7 H7 0.93 . ?
C8 C9 1.385(2) . ?
C8 H8 0.93 . ?
C9 C10 1.374(2) . ?
C10 C11 1.3704(19) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.362(2) . ?
C12 C16 1.391(2) . ?
C13 C14 1.364(2) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?
C15 C16 1.388(2) . ?
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 1.95 2.7707(15) 176.1 . yes
O2 H2A N4 0.82 1.97 2.7895(15) 176.8 2_667 yes
