#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558208.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_1558208
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 H15.02 N2 O2'
_chemical_formula_weight         291.34
_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             2020-04-01T17:48:51-00:00
_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                92.7279(8)
_cell_angle_beta                 107.7404(9)
_cell_angle_gamma                114.3479(10)
_cell_formula_units_Z            2
_cell_length_a                   8.18944(9)
_cell_length_b                   9.87060(10)
_cell_length_c                   10.93717(11)
_cell_measurement_reflns_used    16506
_cell_measurement_temperature    270(2)
_cell_measurement_theta_max      76.821
_cell_measurement_theta_min      4.314
_cell_volume                     751.727(16)
_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 0.996
_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      0.0605864
_diffrn_orient_matrix_UB_12      0.0567472
_diffrn_orient_matrix_UB_13      0.1479403
_diffrn_orient_matrix_UB_21      -0.0025673
_diffrn_orient_matrix_UB_22      -0.1526726
_diffrn_orient_matrix_UB_23      0.0263459
_diffrn_orient_matrix_UB_31      0.2125083
_diffrn_orient_matrix_UB_32      0.0635357
_diffrn_orient_matrix_UB_33      0.0140761
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.965
_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            28258
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.38
_diffrn_reflns_theta_min         4.331
_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  0.77118
_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    1.288
_exptl_crystal_description       irregular
_exptl_crystal_F_000             307
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.115
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.0045(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   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3094
_refine_ls_number_restraints     567
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0344
_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)+(0.0532P)²+0.0526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1005
_reflns_Friedel_coverage         0
_reflns_number_gt                2770
_reflns_number_total             3094
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           BE50_BA50_270
_cod_original_cell_volume        751.727(15)
_cod_database_code               1558208
_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 0.16832(10) 0.14806(9) 0.30449(7) 0.0586(2) Uani 1 1 d . . . . .
H1 H 0.20096 0.174693 0.383823 0.088 Uiso 1 1 calc R U . . .
O2 O 0.81797(11) 0.22017(10) 0.43166(7) 0.0669(2) Uani 1 1 d . . . . .
H2A H 0.822834 0.256186 0.502556 0.1 Uiso 1 1 calc R U . . .
N1 N 0.26200(13) 0.24281(11) -0.43200(8) 0.0586(2) Uani 1 1 d . . . . .
C1 C 0.31831(14) 0.14752(10) 0.27600(9) 0.0471(2) Uani 1 1 d . . . . .
C2 C 0.49288(14) 0.18303(10) 0.37285(9) 0.0472(2) Uani 1 1 d . . . . .
H2 H 0.509132 0.207174 0.460348 0.057 Uiso 1 1 calc R U . . .
C3 C 0.64393(15) 0.18281(11) 0.34010(9) 0.0508(2) Uani 1 1 d . . . . .
C4 C 0.61854(18) 0.14387(12) 0.20914(10) 0.0595(3) Uani 1 1 d . . . . .
H4 H 0.718004 0.141792 0.186184 0.071 Uiso 1 1 calc R U . . .
C5 C 0.44387(19) 0.10857(13) 0.11444(10) 0.0633(3) Uani 1 1 d . . . . .
H5 H 0.426885 0.08309 0.02697 0.076 Uiso 1 1 calc R U . . .
C6 C 0.29301(17) 0.10980(12) 0.14527(10) 0.0574(3) Uani 1 1 d . . . . .
H6 H 0.176259 0.085759 0.079562 0.069 Uiso 1 1 calc R U . . .
C7 C 0.19711(16) 0.14774(12) -0.35664(10) 0.0576(3) Uani 1 1 d . . . . .
H7 H 0.154797 0.04472 -0.385174 0.069 Uiso 1 1 calc R U . . .
C8 C 0.18938(16) 0.19378(12) -0.23911(10) 0.0550(3) Uani 1 1 d . . . . .
H8 H 0.141948 0.122866 -0.190216 0.066 Uiso 1 1 calc R U . . .
C9 C 0.25281(14) 0.34689(12) -0.19367(9) 0.0500(2) Uani 1 1 d D U . . .
C10 C 0.32584(16) 0.44698(12) -0.26977(11) 0.0583(3) Uani 1 1 d . . . . .
H10 H 0.374112 0.550969 -0.241914 0.07 Uiso 1 1 calc R U . . .
C11 C 0.32590(16) 0.39044(13) -0.38679(11) 0.0609(3) Uani 1 1 d . . . . .
H11 H 0.373118 0.458771 -0.437605 0.073 Uiso 1 1 calc R U . . .
C12A C 0.2187(14) 0.3790(7) -0.0670(7) 0.0432(11) Uani 0.443(3) 1 d D U P A 1
H12A H 0.163093 0.298339 -0.028722 0.052 Uiso 0.443(3) 1 calc R U P A 1
C13A C 0.2664(5) 0.5185(3) -0.0109(3) 0.0401(6) Uani 0.443(3) 1 d D U P A 1
H13A H 0.326013 0.596927 -0.049816 0.048 Uiso 0.443(3) 1 calc R U P A 1
C12B C 0.262(6) 0.4531(18) -0.086(2) 0.052(3) Uani 0.067(3) 1 d D U P A 2
H12B H 0.321957 0.555806 -0.087402 0.062 Uiso 0.067(3) 1 calc R U P A 2
C13B C 0.198(4) 0.4199(14) 0.008(2) 0.049(3) Uani 0.067(3) 1 d D U P A 2
H13B H 0.133743 0.316834 0.006856 0.059 Uiso 0.067(3) 1 calc R U P A 2
C14A C 0.2331(13) 0.5618(7) 0.1097(6) 0.0390(11) Uani 0.443(3) 1 d DG U P A 1
C15A C 0.1511(13) 0.4534(6) 0.1775(7) 0.0465(13) Uani 0.443(3) 1 d G U P A 1
H15A H 0.116333 0.351858 0.148786 0.056 Uiso 0.443(3) 1 calc R U P A 1
C16A C 0.1210(14) 0.4968(8) 0.2883(7) 0.0473(14) Uani 0.443(3) 1 d G U P A 1
H16A H 0.066094 0.424286 0.333695 0.057 Uiso 0.443(3) 1 calc R U P A 1
N2A N 0.1729(14) 0.6486(9) 0.3313(7) 0.0468(16) Uani 0.443(3) 1 d G U P A 1
C17A C 0.2549(14) 0.7570(7) 0.2635(8) 0.0479(13) Uani 0.443(3) 1 d G U P A 1
H17A H 0.289656 0.858508 0.292281 0.057 Uiso 0.443(3) 1 calc R U P A 1
C18A C 0.2850(13) 0.7136(6) 0.1527(7) 0.0471(12) Uani 0.443(3) 1 d G U P A 1
H18A H 0.339896 0.786084 0.107371 0.057 Uiso 0.443(3) 1 calc R U P A 1
C14B C 0.2139(11) 0.5251(6) 0.1211(6) 0.0495(12) Uani 0.557(3) 1 d D U P A 2
C15B C 0.1273(11) 0.4422(7) 0.2014(7) 0.0547(11) Uani 0.557(3) 1 d . U P A 2
H15B H 0.078768 0.337099 0.185889 0.066 Uiso 0.557(3) 1 calc R U P A 2
C16B C 0.1138(13) 0.5167(8) 0.3043(7) 0.0549(11) Uani 0.557(3) 1 d . U P A 2
H16B H 0.05406 0.45708 0.355793 0.066 Uiso 0.557(3) 1 calc R U P A 2
N2B N 0.1756(13) 0.6613(9) 0.3367(7) 0.0591(15) Uani 0.557(3) 1 d . U P A 2
C17B C 0.2565(13) 0.7362(7) 0.2604(8) 0.0610(13) Uani 0.557(3) 1 d . U P A 2
H17B H 0.305206 0.841155 0.280768 0.073 Uiso 0.557(3) 1 calc R U P A 2
C18B C 0.2789(10) 0.6799(6) 0.1540(7) 0.0532(11) Uani 0.557(3) 1 d . U P A 2
H18B H 0.336872 0.744271 0.104327 0.064 Uiso 0.557(3) 1 calc R U P A 2
C19 C 0.2504(12) 0.4103(8) -0.0784(8) 0.0572(15) Uani 0.49 1 d D U P A 2
C20 C 0.2364(6) 0.4646(6) 0.0132(4) 0.0600(9) Uani 0.49 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
-1 1 2 0.1024
-2 2 -6 0.081
-4 -1 0 0.0438
5 -1 -3 0.0658
1 -6 4 0.0337
4 1 0 0.0468
-2 -4 4 0.0464
-5 0 4 0.0804
-5 1 -1 0.0444
-3 2 -4 0.0582
-1 -5 -1 0.0561
1 5 1 0.0835
5 -3 0 0.0435
-2 6 2 0.0954
4 -6 1 0.0427
0 -6 2 0.0367
-2 -5 3 0.0426
3 4 -3 0.0582
-1 -1 7 0.0957
-4 -2 1 0.0435
-1 6 0 0.0733
-2 4 -5 0.054
4 2 -4 0.0654
-1 5 -4 0.0508
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 116.81(9) . . ?
O1 C1 C2 121.93(8) . . ?
O1 C1 C6 118.16(9) . . ?
C2 C1 C6 119.91(10) . . ?
C1 C2 C3 120.40(9) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.17(8) . . ?
O2 C3 C4 118.01(9) . . ?
C2 C3 C4 119.82(10) . . ?
C5 C4 C3 118.87(10) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.01(9) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.98(10) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.42(10) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.54(10) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 117.35(9) . . ?
C10 C9 C19 116.5(3) . . ?
C8 C9 C19 126.2(3) . . ?
C10 C9 C12B 101.0(6) . . ?
C8 C9 C12B 141.5(6) . . ?
C19 C9 C12B 15.8(5) . . ?
C10 C9 C12A 129.2(2) . . ?
C8 C9 C12A 113.3(2) . . ?
C11 C10 C9 119.04(10) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N1 C11 C10 123.79(10) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13A C12A C9 121.7(4) . . ?
C13A C12A H12A 119.1 . . ?
C9 C12A H12A 119.1 . . ?
C12A C13A C14A 126.0(4) . . ?
C12A C13A H13A 117 . . ?
C14A C13A H13A 117 . . ?
C13B C12B C9 128.2(14) . . ?
C13B C12B H12B 115.9 . . ?
C9 C12B H12B 115.9 . . ?
C12B C13B C14B 129.1(12) . . ?
C12B C13B H13B 115.4 . . ?
C14B C13B H13B 115.4 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 121.3(4) . . ?
C18A C14A C13A 118.7(4) . . ?
C16A C15A C14A 120 . . ?
C16A C15A H15A 120 . . ?
C14A C15A H15A 120 . . ?
C15A C16A N2A 120 . . ?
C15A C16A H16A 120 . . ?
N2A C16A H16A 120 . . ?
C16A N2A C17A 120 . . ?
N2A C17A C18A 120 . . ?
N2A C17A H17A 120 . . ?
C18A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C15B 114.8(3) . . ?
C18B C14B C20 119.8(4) . . ?
C15B C14B C20 125.4(4) . . ?
C18B C14B C13B 134.6(7) . . ?
C15B C14B C13B 110.3(6) . . ?
C20 C14B C13B 15.5(5) . . ?
C16B C15B C14B 119.3(3) . . ?
C16B C15B H15B 120.4 . . ?
C14B C15B H15B 120.4 . . ?
N2B C16B C15B 126.5(3) . . ?
N2B C16B H16B 116.8 . . ?
C15B C16B H16B 116.8 . . ?
C16B N2B C17B 113.0(3) . . ?
N2B C17B C18B 127.8(4) . . ?
N2B C17B H17B 116.1 . . ?
C18B C17B H17B 116.1 . . ?
C17B C18B C14B 118.6(3) . . ?
C17B C18B H18B 120.7 . . ?
C14B C18B H18B 120.7 . . ?
C20 C19 C9 175.0(9) . . ?
C19 C20 C14B 178.2(7) . . ?
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 1.3581(12) . ?
O1 H1 0.82 . ?
O2 C3 1.3536(13) . ?
O2 H2A 0.82 . ?
N1 C7 1.3311(14) . ?
N1 C11 1.3367(15) . ?
C1 C2 1.3847(14) . ?
C1 C6 1.3896(13) . ?
C2 C3 1.3894(14) . ?
C2 H2 0.93 . ?
C3 C4 1.3938(14) . ?
C4 C5 1.3756(17) . ?
C4 H4 0.93 . ?
C5 C6 1.3806(17) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.3713(14) . ?
C7 H7 0.93 . ?
C8 C9 1.3873(14) . ?
C8 H8 0.93 . ?
C9 C10 1.3860(16) . ?
C9 C19 1.390(8) . ?
C9 C12B 1.500(17) . ?
C9 C12A 1.538(7) . ?
C10 C11 1.3719(16) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12A C13A 1.325(8) . ?
C12A H12A 0.93 . ?
C13A C14A 1.504(6) . ?
C13A H13A 0.93 . ?
C12B C13B 1.291(18) . ?
C12B H12B 0.93 . ?
C13B C14B 1.513(17) . ?
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 C18B 1.381(4) . ?
C14B C15B 1.384(5) . ?
C14B C20 1.393(6) . ?
C15B C16B 1.372(5) . ?
C15B H15B 0.93 . ?
C16B N2B 1.291(4) . ?
C16B H16B 0.93 . ?
N2B C17B 1.293(4) . ?
C17B C18B 1.361(4) . ?
C17B H17B 0.93 . ?
C18B H18B 0.93 . ?
C19 C20 1.172(8) . ?
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 2.7520(11) 175.4 1_556 yes
O2 H2A N2A^a 0.82 1.99 2.81(4) 176.4 2_666 yes
O2 H2A N2B^b 0.82 1.9 2.716(5) 177.8 2_666 yes
